SU498912A3 - Способ получени триазолотиазоловых эфиров кислот фосфора - Google Patents
Способ получени триазолотиазоловых эфиров кислот фосфораInfo
- Publication number
- SU498912A3 SU498912A3 SU1470853A SU1470853A SU498912A3 SU 498912 A3 SU498912 A3 SU 498912A3 SU 1470853 A SU1470853 A SU 1470853A SU 1470853 A SU1470853 A SU 1470853A SU 498912 A3 SU498912 A3 SU 498912A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- triazolothiazole
- dried
- filtered
- suction
- hours
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 5
- 150000002148 esters Chemical class 0.000 title claims 2
- 150000003017 phosphorus Chemical class 0.000 title claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- 239000002244 precipitate Substances 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 150000003385 sodium Chemical class 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 239000012362 glacial acetic acid Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- -1 phosphorus fatty acids Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 235000011121 sodium hydroxide Nutrition 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Description
перемешивают 3 час при 40-50° С, выливают в воду, экстрагируют бензолом, высушивают экстракт, уиаривают, нагревают остаток в вакууме и получают 68 г (78%) О-этилэтанО- (З-метил) - 1,2,4 - триазоло-6-ил- 2,3-Ь - тиазолового эфира тиофосфоновой кислоты, 1,5610.
Вычислено, %: S 22; мол. вес. 291.
С НиНзОзРЗг.
Найдено, %: S 22,12.
Дл синтеза исходного 3-.метил-6-окси-1,2, 4-триазоло - 2,3-6 - тиазола раствор 50 г (0,4 моль) веш,ества формулы
., N-M-(
I j
S
-Ч
Claims (2)
- SH в 400 мл 1 п. едкого натра смешивают с 40 г метилового эфира хлоругольной кислоты при 20-30° С, перемешивают 2 час, отсасывают осадок, высушивают п получают соединение формулы -N-NHj- HCJ и Выход 60%, т. пл. 150° С. 80 г полученного соединени в 400 мл бензола и 0,4 моль метилата натри перемешивают 12 час при 50° С, охлаждают, смешивают с эфиром, отсасывают, высушивают и получают кристаллы 64 г (90%) натриевого производного формулы -N-N Вычислено, %: Na 13; мол. вес 177. C5H4NaN30S. Найдено, %: Na 13,04. 36 г (0,2 моль) натриевого нроизводного раствор ют в 50 мл воды, добавл ют 12 г лед ной уксусной кислоты, выдерживают 9 час при 0° С, отсасывают осадок, перекристаллизовывают из смеси метиловый спирт- ацетон и получают 3-метил-6-окси-1,2,4-триазоло-| 2 ,3-6 -тиазол, выход 50%, т. нл. 181° С. Аналогичным образом получают триазолотиазоловые эфиры кислот фосфора, указанные в таблице. Показатель преломлени определен при 21° С. Формула изобретени 1. Способ получени триазолотиазоловых фиров кислот фосфора общей формулы где R и R - алкил, алкоксил или алкиламиногруппа , содержащие 1-б атомов углерода, или фенил, X - О или S, отличающийс тем, что хлорангидриды кислот фосфора общей формулы где R, R и X имеют вышеуказанные значени , подвергают взаимодействию с 3-метил6-окси-1 ,2,4-триазоло - 2,3-& -тиазолом в присутствии акцептора кислоты в среде инертного органического растворител с последующим выделением целевого продукта известными приемами.
- 2. Способ по п. 1, отличающийс тем, что процесс провод т при 40-50° С.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691942015 DE1942015C3 (de) | 1969-08-19 | Triazolo-thiazol (th'iono)-phosphor (phosphon)-säureester, Verfahren zu ihrer Herstellung sowie diese enthaltende Mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU498912A3 true SU498912A3 (ru) | 1976-01-05 |
Family
ID=5743135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1470853A SU498912A3 (ru) | 1969-08-19 | 1970-08-13 | Способ получени триазолотиазоловых эфиров кислот фосфора |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3682943A (ru) |
| JP (1) | JPS553325B1 (ru) |
| AT (1) | AT296338B (ru) |
| BE (1) | BE755028A (ru) |
| CA (1) | CA938613A (ru) |
| CH (1) | CH538513A (ru) |
| CS (1) | CS164281B2 (ru) |
| DK (1) | DK126505B (ru) |
| EG (1) | EG10292A (ru) |
| ES (1) | ES382819A1 (ru) |
| FR (1) | FR2059010A5 (ru) |
| GB (1) | GB1269488A (ru) |
| IL (1) | IL34985A (ru) |
| NL (1) | NL166264C (ru) |
| PL (1) | PL80994B1 (ru) |
| RO (1) | RO62237A (ru) |
| SU (1) | SU498912A3 (ru) |
| TR (1) | TR16583A (ru) |
| ZA (1) | ZA705066B (ru) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3948926A (en) * | 1971-12-30 | 1976-04-06 | Saburo Kano | O,O-Diethyl-2-(5-ethyl-6-bromothiazolo[3,2-b]-s-triazolyl)thionophosphate |
| JPS4932873B2 (ru) * | 1971-12-30 | 1974-09-03 | ||
| US3970751A (en) * | 1972-12-29 | 1976-07-20 | Nippon Soda Company Limited | Certain thiazolotriazolyphosphonothioates used as insecticides |
| US4024252A (en) * | 1973-04-07 | 1977-05-17 | Nippon Soda Company Limited | 2-(5-Ethyl-6-bromothiazolo[3,2-b]-5-triazolyl)thiophosphonate esters, compositions and method of use |
| DE2350631C2 (de) * | 1973-10-09 | 1981-10-15 | Bayer Ag, 5090 Leverkusen | Triazolothiazol-(thiono)-phosphor(phosphon)-säureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide |
| DE2361451C2 (de) * | 1973-12-10 | 1982-06-03 | Bayer Ag, 5090 Leverkusen | Triazolothiazolyl-(thiono)-phosphor (phosphon)-säureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Bekämpfung von Insekten, Milben und Zecken |
| KR0168979B1 (ko) * | 1995-07-12 | 1999-01-15 | 김종인 | 티아졸릴 트리아졸로티아졸 유도체 |
| WO2010036882A1 (en) * | 2008-09-29 | 2010-04-01 | The Hartz Mountain Corporation | Photo-stable pest control |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3428645A (en) * | 1965-10-23 | 1969-02-18 | Stauffer Chemical Co | Phosphorus esters of certain thiazole derivatives |
-
0
- BE BE755028D patent/BE755028A/xx unknown
-
1970
- 1970-07-23 ZA ZA705066A patent/ZA705066B/xx unknown
- 1970-07-24 IL IL34985A patent/IL34985A/en unknown
- 1970-07-29 CH CH1146370A patent/CH538513A/de not_active IP Right Cessation
- 1970-07-29 RO RO64091A patent/RO62237A/ro unknown
- 1970-08-06 GB GB37989/70A patent/GB1269488A/en not_active Expired
- 1970-08-10 CS CS5552A patent/CS164281B2/cs unknown
- 1970-08-11 EG EG361/70A patent/EG10292A/xx active
- 1970-08-12 CA CA090540A patent/CA938613A/en not_active Expired
- 1970-08-12 US US63271A patent/US3682943A/en not_active Expired - Lifetime
- 1970-08-13 SU SU1470853A patent/SU498912A3/ru active
- 1970-08-17 JP JP7145570A patent/JPS553325B1/ja active Pending
- 1970-08-18 DK DK424370AA patent/DK126505B/da unknown
- 1970-08-18 PL PL1970142756A patent/PL80994B1/pl unknown
- 1970-08-18 TR TR16583A patent/TR16583A/xx unknown
- 1970-08-18 ES ES382819A patent/ES382819A1/es not_active Expired
- 1970-08-18 NL NL7012197.A patent/NL166264C/xx not_active IP Right Cessation
- 1970-08-19 FR FR7030520A patent/FR2059010A5/fr not_active Expired
- 1970-08-19 AT AT751870A patent/AT296338B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CS164281B2 (ru) | 1975-11-07 |
| GB1269488A (en) | 1972-04-06 |
| FR2059010A5 (ru) | 1971-05-28 |
| CA938613A (en) | 1973-12-18 |
| ES382819A1 (es) | 1972-11-16 |
| DK126505B (da) | 1973-07-23 |
| NL166264C (nl) | 1981-07-15 |
| TR16583A (tr) | 1973-01-01 |
| DE1942015A1 (de) | 1971-03-04 |
| RO62237A (ru) | 1977-08-15 |
| BE755028A (fr) | 1971-02-19 |
| US3682943A (en) | 1972-08-08 |
| EG10292A (en) | 1976-07-31 |
| IL34985A (en) | 1972-11-28 |
| CH538513A (de) | 1973-06-30 |
| NL166264B (nl) | 1981-02-16 |
| ZA705066B (en) | 1971-04-28 |
| JPS553325B1 (ru) | 1980-01-24 |
| NL7012197A (ru) | 1971-02-23 |
| PL80994B1 (ru) | 1975-08-30 |
| DE1942015B2 (de) | 1977-06-02 |
| AT296338B (de) | 1972-02-10 |
| IL34985A0 (en) | 1970-09-17 |
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